A new general approach for the stereocontrolled synthesis of functionalised γ- and δ-lactams

Daly, M., Gill, K., Sime, M., Simpson, G.L. and Sutherland, A. (2011) A new general approach for the stereocontrolled synthesis of functionalised γ- and δ-lactams. Organic and Biomolecular Chemistry, 9(19), p. 6761. (doi: 10.1039/C1OB05833A)

Abstract

A new flexible approach for the stereoselective synthesis of substituted 1H-pyrrol-2(5H)-ones and 3,6-dihydro-1H-pyridin-2-ones has been developed. The general strategy employed the stereoselective reduction of a series of α,β-unsaturated ketones under chelation control to give the corresponding allylic alcohols. Overman rearrangement to install the key C–N bond followed by conversion to either prop-2-enoyl or but-3-enoyl derivatives and a ring closing metathesis reaction gave the target unsaturated γ- and δ-lactams. The synthetic utility of these compounds as building blocks was demonstrated by the preparation of the N-Boc derivative of (−)-coniine.

• Item Type: Articles
• Status: Published
• Refereed: Yes
• Glasgow Author(s) Enlighten ID: Gill, Miss Kathryn and Sime, Dr Mairi and Sutherland, Professor Andrew and Daly, Mr Mark
• Authors: Daly, M., Gill, K., Sime, M., Simpson, G.L., and Sutherland, A.
• College/School: College of Science and Engineering > School of Chemistry
• Journal Name: Organic and Biomolecular Chemistry
• ISSN: 1477-0520